1. Field of Invention
This invention relates to pyridoindolobenzodiazepines, processes for their preparation and uses as tranquilizers, and more particularly to tetrahydro-, hexahydro-, and octahydropyridoindolobenzodiazepines useful as tranquilizers.
2. Prior Art
Cohen et al., U.S. Pat. Nos. 3,373,168, and 3,457,271, describe compounds which are 1,2,3,4,8,9-hexahydropyrido[4',3':2,3]indolo[1,7-ab][1]benzazepines and 1,2,3,4,4a,8,9,14a-octahydropyrido[4',3':2,3]indolo[1,7-ab][1]benzazepines and their preparation from N-nitrosoiminodibenzyl and 1-alkyl-4-piperidones. ##STR1## The octahydro compounds are said to be antidepressant agents.
Adams, in U.S. Pat. Nos. 3,932,650 and 3,983,123, describes CNS depressant and analgesic 1,2,3,4,4a,8,9,14a-octahydropyrido[4',3':2,3]indolo[1,7-ab][1]benzazepines . These compounds are 4a,14a-trans, while the octahydro compounds of the above patent are of the cis configuration.
Berger, in U.S. Pat. Nos. 3,890,327 and 4,018,930, describes trans-1,2,3,4,4a,8,9,14a-octahydropyrido[4',3':2,3]indolo[1,7-ab][1]benzaz epine and 3-substituted analgesic and sedative/tranquilizer derivatives thereof.
Blumberg, U.S. Pat. No. 3,790,675 and Finizio, U.S. Pat. No. 3,764,684, describe analgesic, antiolytic, and antipsychotic 1,2,3,4,8,9-hexahydropyrido[4',3':2,3]indolo[1,7-ab][1]benzazepines.
A process for preparing these hexahydropyridoindolobenzazepines is claimed in Berger and Teller U.S. Pat. No. 3,829,431. It involves N-nitrosoiminodibenzyl and 4-piperidone or 1-allyl-4-piperidones.
In an article by W. H. Linnell and W. H. Perkin, Jr., J. Chem. Soc., 2451-2460 (1924), the parent, unsubstituted nitroso compound (III) described in the subject application is prepared and reacted with cyclohexanone to give a product with one of the following structures: ##STR2## Linnell et al. preferred the latter structure on the basis of some degradative work, but by analogy to the behavior of 4-piperidone in the present application, the former might be expected to have been the actual product.